


Faith in Self

by CrashDevil (cjdevlin19)



Category: Supernatural
Genre: AU, Angst, CEO Dean Winchester, F/M, Past Cheating, Reader-Insert, Regret, Self-Esteem Issues
Language: English
Status: Completed
Published: 2020-06-08
Updated: 2020-06-08
Packaged: 2021-03-03 20:34:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,183
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24601681
Author URL: https://archiveofourown.org/users/cjdevlin19/pseuds/CrashDevil
Summary: Sequel to Faith in the Unfaithful. Dean’s life has gone steadily downhill since Y/n found him with Nicoletta.~~~~~~~~~~~~~~~~~~~~~~“Yes, sir,” she said, waiting a moment before adding, “Anything else, sir?”He rolled his eyes and shook his head, waving at her to go away. He knew what she wanted, but he hadn’t been able to bring himself to fuck her since his girlfriend found out he was fucking the skinny brunette. Ex-girlfriend. Y/n walked out when Dean admitted he wasn’t attracted to her anymore.He never stopped loving her, though; shouldn’t that count for something?Not according to Dean’s family. They were all on Y/n’s side. They loved her just as much as Dean did, more than according to his brother. They were all very angry at him...and so was he. He’d been so caught up in what his body wanted that he hadn’t considered the fact that he might lose everything...over Nicoletta, who he couldn’t get rid of now without risking a lawsuit. He was stuck with her, with the constant reminder of how he screwed himself out of the greatest thing he ever had.
Relationships: Benny Lafitte/You, Dean Winchester/You
Comments: 4
Kudos: 57





	Faith in Self

**Story Warnings** : angst, mentions of cheating, AU, self-esteem issues, regret, sad!dean (and it’s okay if you don’t feel bad for him lol)

~~~~~~~~~~~~~~~~~~~~~~

Dean rubbed his hand across his forehead as Nicoletta ran through his itinerary for the week. Five days of a conference where he didn’t want to be, filled with people he didn’t want to be around, in a convention center that smelled vaguely of cheese because the last conference held there was a bunch of cheesemakers. But at least it was Vegas. He could go get a drink and a big-ass steak in a strip club and proceed to lose half his net worth at the craps tables if he felt like it. 

“And I just got a confirmation from O’Keefe Biotech that they’re willing to send their new CMO to meet with you about collaborating on their new prothstetics line tomorrow,” Nicoletta said immediately following a ding from her phone.

“Awesome. Set up a time and I’ll be there. That’d be a big win for us so...uh, find out about their new guy. See if it’s someone I can bully or someone I actually have to negotiate with,” he said, loosening his tie and throwing it at the desk chair in his hotel room where his suit jacket was tossed. “And send my jacket to the cleaner downstairs. There was a weird wrinkle in the sleeve all day. Bugged the hell outta me.”

“Yes, sir,” she said, waiting a moment before adding, “Anything  _ else _ , sir?”

He rolled his eyes and shook his head, waving at her to go away. He knew what she wanted, but he hadn’t been able to bring himself to fuck her since his girlfriend found out he was fucking the skinny brunette. Ex-girlfriend. Y/n walked out when Dean admitted he wasn’t attracted to her anymore.

He never stopped loving her, though; shouldn’t that count for something?

Not according to Dean’s family. They were all on Y/n’s side. They loved her just as much as Dean did, more than according to his brother. They were all very angry at him...and so was he. He’d been so caught up in what his body wanted that he hadn’t considered the fact that he might lose everything...over Nicoletta, who he couldn’t get rid of now without risking a lawsuit. He was stuck with her, with the constant reminder of how he screwed himself out of the greatest thing he ever had.

He put on a pair of jeans and a t-shirt and headed for the hotel bar. A bunch of MIT grads hitting on bartenders and cocktail waitresses, a bunch of nerds whose only shot with these women would be if they pulled out a wad of cash. Dean shook his head and took a seat, rolling his eyes at the futile display around him. “Gotta love conventions,” he muttered to himself as the bartender walked up. “Double whiskey, neat.”

“You in town for the convention?” the bartender asked, smiling brightly at him.

“Which one? Aren’t there, like, seven conventions happening every week in Vegas?” he responded with a small smirk.

“I figure you’ve gotta be with the firemen, right?” she said, setting his drink in front of him on the bar.

He laughed and picked up the glass. “Actually, I’m with these nerds,” he said, pointing at a group of bespectacled men laughing in the corner. “The engineering trade conference. It’s a lot more glamorous than it seems...with a lot fewer hose jokes.”

“Well, I’ve never hooked up with an engineer so…” the bartender started before nodding at the napkin in front of him where her number was written. “Text me.”

Dean nodded and took a drink. “Thanks.” He knew he wasn’t going to. Since he blew shit up with Y/n, he'd purposely spent his nights alone. Almost nine months of just him and his hand...and that fleshlight in his suitcase. 

"No, she's fat, but like, she's still hot," a voice behind him said. "She knows how to dress for her figure, she knows how to do her hair and makeup, she's not unapproachable and pretentious. She's not a bitch like my other chick bosses have been. I think I might be able to sleep my way up the ladder, if you know what I mean."

"Your boss is not gonna screw you, dude. She's engaged!"

"Hey! I'm bound to be a better catch than the dude she's seeing. What kinda name is Lafitte? Sounds like an NPC in a old-timey RPG."

"Dude, they've been together for months. You aren't getting in there."

Dean rolled his eyes and gulped down the rest of his whiskey. He was right that this conference was a shitshow and he was bored out of his mind already. Time to head back to the room and pull out his toy.

~~~~~~~~~~~~~~~

"What were you able to find out about the new CMO?" Dean asked the next morning when Nicoletta arrived with his Americano and his freshly-laundered suit jacket.

"Almost nothing. The old one bowed out two weeks ago. They haven't done an announcement on who got the job. They're actually announcing it today...at three."

"And when am I meeting him?" Dean asked, taking a drink of his coffee.

"Noon," she said, a bit apologetically. 

"Great. Love walkin' into a negotiation blind," he responded sarcastically. 

"I'm sorry. They've kept him under wraps until they do the announcement. There was nothing I could do."

"You ask anybody who works under him? You go chat up the nice marketing folks over at O'Keefe's and try to find out, or did you just get on your phone and ask Google, 'cause  _ I  _ coulda done that, Nicki!" he snapped, putting his cup down and slipping his jacket on.

"I'm sorry, okay. I tried to find out!" she responded.

"Well, try harder next time," he snapped, heading to the conference room they agreed to meet in. He sent Nicki out, not wanting to see her anymore. It was a little past noon according to Dean's watch that he kept checking, when the door opened and a man in a suit walked in. Dean stood and offered his hand. "Punctuality isn't a virtue at O'Keefe, I take it."

"Sorry, the CMO got caught on an important phone call to the CFO. You understand, I'm sure," the man shot back, holding the door open and leaving Dean's hand hanging in the air.

"I really did want to be here first," a familiar voice said. Dean's throat went dry and his jaw dropped slightly as Y/n walked in. Her hair was perfect, makeup drawing attention to all the right parts of her gorgeous face. She was wearing a black bodycon dress with a mesh neckline and shiny black stilettos. She had a smile on her face and a large diamond ring on her left ring finger. "But I suppose you wouldn't have gotten to enjoy the whole of the surprise if I were already sitting when you walked in."

It took Dean a minute to come to his senses and drop his hand, licking his lips and swallowing to alleviate the dryness in his throat. " _ You're _ Chief Marketing Officer for O'Keefe?"

"Yep!" she answered proudly, as she sat across from Dean, who looked down at her dumbly for a moment before sitting. "Yeah, Nicki almost ruined the surprise. We're doing the announcement at three and she was  _ trying _ to get this meeting at four." Her assistant whispered in her ear and she laughed before waving her hand. "We're good. Go get yourself a coffee, Jake. I'll call when we're done here."

There was a long moment of awkward silence before he cleared his throat. "You, uh, you look good. You look  _ great _ . You-"

"No, I haven't lost any weight. Still exactly as big as I was when I got back from New York," she interrupted.

"I wasn't gonna ask that," he defended. "I just...you never...looked like that when we were together."

"It's confidence. It's slimming."

Dean was totally thrown. This seemed almost like a completely different woman than the one he ran out of his life. "H-how did you even get this job? A year and a half ago, you were a damn Customer Service Rep."

She laughed and ran her tongue along the inside of her cheek. "It's a pretty funny story, actually. See, I've got  _ you _ to thank for this. Sending me to that extensive marketing training in New York looked amazing on my CV. It got me a job as VP of Marketing for O'Keefe and when Jackson stepped down after the heart attack, I was the natural choice. Your philandering put me here. Isn't that funny, Dean?"

"Hilarious," he said, his chest filling up with angry fire.

"Oh, and my fiance works at O'Keefe too, so you chasing me off from Sanderson put me on the path to meet  _ him _ , too. Isn't that great?" 

He wanted to be upset about the giddiness in her voice but he pushed it down. Him cheating on her had obviously been the absolute best thing he'd ever done for her. She was allowed to be happy about the irony of that. "Okay, well, let's...let's do this," he said, flipping open a folder and trying to move forward with the meeting.

"Yeah, no. Here." She slid her own folder across the table. "This is what we're offering. 60-40 on our benefit, everything goes through our Research, nothing happens unless it's approved by our entire board, and the Sanderson logo is going to occupy a third the space of the O'Keefe logo on all marketing. Take it or leave it."

"What?! That's ridiculous! We're gonna be doing all the work!" he shouted, jumping up out of his seat. She just bit her thumbnail and waited for him to calm down. "That's not a fair deal at all."

"You realize that we are at a conference of engineering companies, right?" she said, boredly. "The only reason I agreed to meet with you instead of taking that deal straight to Gordon at Walker Initiatives is because it was  _ you _ . I guarantee Gordon would take that deal."

"Gordon Walker makes Elon Musk seem sane! You can't do business with him!"

"Gordon Walker gets things done; on time and under budget,” she pointed out. “If he’s a bit psycho, does that really matter when there’s billions on the line? You’re a fat-shaming, philandering piece of shit, I’m still willing to work with  _ you _ .”

“This is revenge, isn’t it? This...this isn’t even a  _ deal _ ! It’s a--this is a--this isn’t fair!”

Y/n sighed and set her hand on the folder, giving him a tight smile as she stood. “I told my CEO you were gonna be too blinded by our past to see this as a perfectly fine deal.”

Dean set his hand on top of hers to keep her from walking out, fear of losing a multibillion dollar contract stopping him. “Let me present it to the board.”

“Are you CEO or not, Winchester?” she asked.

“Not for very much longer if I fuck this up. Give me twenty-four hours to run it by ‘em.”

She smiled and pulled her hand away. “I’ll give ya thirty-six. Midnight tomorrow.”

“Thank you,” Dean said, grabbing the folder.

“Hey, since I know you’re gonna be in for the whole convention, why don’t you come to dinner with me and my fiance? You can bring Nicoletta! It’ll be a double date!” Dean wanted to punch something at the idea of going on a double date with his ex and the woman he cheated on her with, but he just nodded. He had to meet the man who had swept Y/n off of her feet and instilled this confidence in her. "I'll have my assistant set it up with your girl. See ya tonight, Dean."

~~~~~~~~~~~~~~~~~~~~~

Dean didn’t watch the big announcement. He disappeared into his hotel room and started drinking from the minibar. “She’s...doing so well for herself, Sammy. She’s...she looks so good and she’s...she’s engaged and-”

“I know,” Sam’s voice filtered through the speaker of Dean’s phone and the intoxicated Winchester sat up to glare at the screen.

“What do you mean, you know?”

“She invited me to the wedding, Dean. Dad, too.”

“What?!” Dean barked.

“They haven’t done official invites yet, but she told me that Ben was okay with us coming. I didn’t stop being friends with her just because you were an asshole, Dean.”

“You knew she was getting married and you didn’t think to tell me?!” Dean snapped.

“I didn’t think it was your business, dude. When you see her, tell her I said ‘Congratulations’ on the promotion, will you?” Sam said before hanging up the phone.

Dean scoffed and stared at the phone for a few minutes before getting up to take a shower and get ready for dinner. “You’re not goin’,” he snapped at Nicoletta as soon as she arrived at his door.

“What do you mean? She  _ invited  _ me!”

“She invited you to make us uncomfortable,” Dean responded. “And I’d rather be uncomfortable by my damn self than next to you. I’ll see you in the morning, Nicki.” She just stared after him as he walked down the hall to the elevators. He leaned his head back against the wall of the elevator as he rode it down to the lobby. He wasn’t looking forward to meeting Y/n’s fiance. It was like a slap in the face. It was a man sitting there saying, ‘Hey, man, you fucked up and let this amazing woman get away. This is how I’ve been doing it better than you.’

When he arrived at the restaurant, he gave his name and the hostess guided him toward a table. He could see Y/n across the restaurant, wearing an elegant red dress with long lace sleeves. She was sitting at a table with a man but Dean couldn’t see his face because he was approaching from behind him. Y/n noticed Dean as he got close and she pointed him out. She and her fiance both stood and when the man turned to greet him, Dean’s jaw dropped.

“Benny?!” Dean exclaimed.

Y/n’s eyes went wide as the men stared at each other. “Y-you two know each other?” she asked, all the sass and confidence draining out of her in that instant.

“Yeah. Dean an’ I was at MIT same time. We’s like brothers,” the blue-eyed man answered, eyes narrowing at the other man.

“We talk at least twice a month,” Dean said, feeling completely betrayed. “How did I not know you were dating my ex-girlfriend?”

“How’d I not know you was da one cheated on her and made ‘er feel ugly, huh?” Benny returned. “You never tol’ me the name’a the girl you screwed the pooch with.”

“And you’ve never told me the name of the amazing woman you met at work. You  _ also _ didn’t tell me you friggin’  _ proposed _ to her!”

“I haven’t got you on the phone in two weeks, brother. We been busy.”

“She had time to tell  _ Sam  _ that you proposed and you didn’t have time to tell  _ me _ ?”

“Boys, sit down, people are staring,” Y/n snapped, moving the skirt of her dress out of the way and taking her seat. Benny returned to his seat and Dean took the one across from him, directly next to Y/n. She picked up the menu and flipped to the wine list, sighing. “This was not expected.”

“No shit,” Dean grumbled, picking up his own menu.

“Where’s Nicoletta?” Y/n asked quietly.

“I’m not...Back at the hotel, probably. I didn’t want her here,” Dean answered.

“Why not?” Y/n asked, deciding on a red wine.

“He’s not dating Nicki. He don’t even like her,” Benny responded for Dean.

“I’d have fired her months ago if I had a reason better than ‘she reminds me of the worst decision I ever made’,” Dean said, sneaking a look at Y/n. She looked uncomfortable. At least he wasn't the only one.

"That was a series of decisions, Dean," Y/n said, eyes on the steaks section of the menu.

"You're not wrong. It was a  _ series  _ of the worst decisions I ever made."

"You know she lost thirty pounds bef-" Benny started but Y/n reached out and grabbed his hand.

"Don't. It doesn't matter. I didn't lose the weight for him.” Benny covered her hand with his free one. “Thirty pounds wasn’t enough to make me look like Nicki, so it wouldn’t have made any difference anyway. Whether I caught him in flagrante delicto or not.”

Dean groaned and rubbed at his eyes. “Look, I get it, I’m a piece of shit. But I wasn’t trying to hurt you, okay? I loved you. That’s why I didn’t tell you to lose weight. I didn’t want you to think you had to be skinny to be my girlfriend.”

Y/n’s eyes snapped to his and narrowed. “But I had to be skinny to not get cheated on? I had to be skinny to have you present when we were in bed together? I had to be skinny to be desirable? You know, I was fat the entire time you knew me, Dean. I was fat when you walked up to me at that party. If it was such a  _ problem _ for you, why the hell did you ever talk to me?”

“It wasn’t a problem until I saw you naked!” Dean snapped in a whisper. “And by the time you and I hit the mattress, I was already in love, my brother and dad were practically writing my vows for me, and I figured I could live with it.”

“But you couldn’t. You couldn’t live with it and instead of being a man and saying something...instead of confronting a problem, you caused more problems.” Y/n shook her head and took a drink of the water on the table in front of her. “You know...if I were less of a stubborn bitch, you might’ve broken me. If I hadn’t been so determined to stay true to myself, I might have fallen to body dysmorphia, become obsessed with fitting into  _ your  _ vision of beauty...I might have gotten saddled with an eating disorder.”

“Issa good thing you too stubborn to lay down, huh, cher?” Benny said, bringing her hand to his lips to kiss her knuckles.

She smiled softly and nodded. “It’s a good thing that I found a man who knows that love doesn’t mean anything if it’s loving pieces of me, not the whole.”

Benny leaned over and pressed a kiss to her cheek. “You know I’m da luckiest man in da world, baby.”

Dean looked away, closing his eyes. He sighed and stood and the couple looked up at him. “Look, I’m sorry. I thought I could do this, but I can’t. Congratulations on the engagement. I’m sorry.” 

Benny followed Dean out of the restaurant, stopping him before he could get to the curb to hail a taxi. “Brother, I don’t know what to do here. I was gonna ask you to be in da wedding, but that’s outta da question now, ain’ it?” Dean rolled his eyes and turned to glare at the Cajun, who was glaring right back. “Seriously, you know how many times I cursed you the last six months, Dean? That woman in dare is actin’ like the HBiC but she cry ‘cause’a you every damn day. Yeah, she’s happy wit’ me, but you cut her deep an’ that ain’t healed. That ain’t even scarred over yet. It’s an open wound she rips the sutures outta every time she look in da mirror.”

Benny stepped closer to Dean, running his fingers across his beard. “She don’t think she’s pretty. She don’t think she’s worthy. She won’t turn the lights on, brother, and that’s on you.”

“I fucked up, Benny. What do you want me to say? I’ve apologized. I regret it deeply. I tried to get her to stay, I tried to get her to talk to me so that we could work through it and she left-”

“Did you really expect her to stay wit’chu after you cheated on her? After you tol’ her you hated her body? Her body is amazing, by the way. She’s soft and warm and she’s tight in the right places. How could you look at those breasts and  _ not _ love them?”

“Like I said, I fucked up! I hurt her and I hurt myself and I hate that I did it. What do you want me to say?”

Benny sighed and shoved his hands in his pockets. “I don’t know.” He shook his head. “I don’t rightly know. But safe to say...we gonna have to work some shit out if you wanna be part of my life, since she is in my life for the rest of it.”

Dean nodded. “Yeah. Understandable. I’ll call you.” Benny nodded and headed back into the restaurant. 

When he got back to the hotel, there was an envelope on the desk in his room. He sighed as he opened it and read ' **I am emailing the official version to HR but please consider this my resignation. I'm done being treated like shit because you regret sleeping with me. I quit.'**

"Awesome," he grumbled, flinging the letter at the desk and heading to the minibar again. He'd managed to fuck up everything in his life. He wasn’t sure how he was going to make it through the rest of the week, let alone the rest of his life.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“I’m proud of you. You’re here, you’re sober, you look presentable. If you get through the objections part without making an ass of yourself, I’ll give you a shiny gold star sticker,” Sam said, condescendingly.

“Aren’t you supposed to be ushering something?” Dean grumbled, thinking about the flask in his pocket that he was specifically holding back from so as to avoid making an ass of himself.

“Look, don’t get pissy with me because Benny picked up the pieces you left behind.”

“I’m pissy because you’re my brother and you’re participating in one of my best friends marrying the woman I love. Do I not have the right to?”

“Do you just block out the part of the story where you sent her to New York specifically to get your dick wet for six  _ months _ and couldn’t even be bothered to pick her up the day she got back because you were too busy having one last fling with your assistant? That you lied to me about that meeting so that I would lie to her for you? Screw you, Dean. You don’t have a right to be pissy about anything. You deserve this.” Sam pointed at the altar, where Benny was standing with the priest, looking excited and nervous in his tuxedo. “And she deserves this. She deserves this day to go off without a hitch, so if I see you pull out that flask, I’m gonna usher you out of this damn church.”

Dean rolled his eyes as his brother walked away. He didn’t block out any part of the story. He had no delusions that he was the reason the Cajun was awkwardly fiddling with his cummerbund at the altar of the church where Y/n’s parents got married. He knew he’d massively messed up. As long as she was happy now, right?

He clenched his teeth together and took a deep breath as the music started. Flower girl, ring-bearer, bridesmaid, bridesmaid, maid of honor...Y/n. “Fuck,” he whispered as she walked in. Tears welled up in his eyes at her beauty. How could he have ever thought that Nicoletta was more attractive? Y/n looked like a damn angel in white.

He leaned all of his weight against the back wall of the church and watched as his friend said his vows. Y/n was glowing. Benny kept wiping overwhelmed tears from his eyes. It was a picture-perfect ceremony, right down to the perfect kiss.

Dean caught Benny’s eyes as the newlyweds ran down the aisle and all Dean could do was nod at his friend. Sam and John walked up to Dean as everyone followed the couple out of the church. “Still sober, I see,” Sam said.

“Yeah,” Dean grunted, giving the other Winchesters a tight smile before reaching into his jacket and pulling out his flask. “Not for long,” he said before walking out and heading to his car. Sam and John followed him. 

“Are you going to the reception, son?”

“Nope. Can’t watch the dance and the cake smashing and the...happy. I’ll be just fine with my baby and my bourbon. Give the newlyweds my regards,” Dean said, pulling open the driver’s side of his classic Impala.

“Don’t do anything stupid, Dean,” Sam called out as Dean turned over the engine.

“Can’t do anything stupider than what I’ve done,” he muttered before speeding off out of the parking lot.


End file.
